Obsession isn't a bad thing in this case as long as you don't make poor decisions just to "get in the game"It sounds like your motive to get in real estate is a good one if you are looking to help other people.

Most S8 tenants have a history of bad decisions, often having convictions, evictions, bankruptcies, chargeoffs, collections, garnishments, etc.

This not only preserves the value of your investment but also enhances its profitability over time.Also, I'd like to emphasize the importance of understanding the local market dynamics, which will help you make informed decisions about where to buy, what to buy, and at what price.

So my best advice would be to not make a clear cut decision yet, but keep your eyes open for an opportunity that gets you there.

There are a lot of poor operators out there but there's also a lot of good ones.

What information I should be analyzing to help me make a decision on where I should start.  

I seem to remember that I didn't even have a business card until then either.You are VERY late to the game to be making these decisions. 

Guess I'm looking to make the best decision with the money.

I would look at the value of the rentals before you make a decision to see if that makes sense for you.Regarding the furnishings, if you have to pay more for them (again here in FL, properties are generally listed fully furnished and you don't really get a discount to tell people to take the crap out - in fact, I had one guy refuse a good offer because one of my conditions was for them to take their crap!  

For every good matching comp at a high price theres 16 poor priced matching comps that the appraisers only focus on.